Portland (PDX) to Chicago (ORD) · Dec 27, 2026 · one way

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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Route overview: Portland to Chicago (ORD) flight deals

2026-12-27 · one way · Axel-exclusive $256.50

• Alaska Airlines AS324: PDX 2026-12-27 07:00:00 → ORD 2026-12-27 13:10:00; nonstop; 250 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $263.25

• American Airlines AA3329: PDX 2026-12-27 23:31:00 → ORD 2026-12-28 05:25:00; nonstop; 234 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $276.75

• United Airlines UA2306: PDX 2026-12-27 07:02:00 → ORD 2026-12-27 13:06:00; nonstop; 244 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $270.00

• Delta Air Lines DL1203 / DL2377: PDX 2026-12-27 09:59:00 → ORD 2026-12-27 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2026-12-27 09:59:00 → SLC 2026-12-27 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2026-12-27 13:55:00 → ORD 2026-12-27 18:06:00.

2026-12-27 · one way · Axel-exclusive $263.25

• American Airlines AA562: PDX 2026-12-27 13:22:00 → ORD 2026-12-27 19:44:00; nonstop; 262 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $276.75

• United Airlines UA2266: PDX 2026-12-27 14:34:00 → ORD 2026-12-27 20:40:00; nonstop; 246 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $243.00

• American Airlines AA2496 / AA2221: PDX 2026-12-27 14:36:00 → ORD 2026-12-27 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-12-27 14:36:00 → DFW 2026-12-27 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-12-27 21:30:00 → ORD 2026-12-27 23:59:00.

2026-12-27 · one way · Axel-exclusive $249.75

• Alaska Airlines AS3355 / AA3186: PDX 2026-12-27 07:16:00 → ORD 2026-12-27 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-12-27 07:16:00 → SLC 2026-12-27 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-12-27 11:37:00 → ORD 2026-12-27 16:00:00.

2026-12-27 · one way · Axel-exclusive $249.75

• Alaska Airlines AS250 / AA677: PDX 2026-12-27 10:30:00 → ORD 2026-12-27 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-12-27 10:30:00 → GEG 2026-12-27 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-12-27 14:13:00 → ORD 2026-12-27 20:07:00.

2026-12-27 · one way · Axel-exclusive $256.50

• United Airlines UA459 / UA2329: PDX 2026-12-27 05:00:00 → ORD 2026-12-27 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-12-27 05:00:00 → DEN 2026-12-27 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-12-27 09:55:00 → ORD 2026-12-27 13:35:00.

2026-12-27 · one way · Axel-exclusive $256.50

• United Airlines UA1292 / UA1958: PDX 2026-12-27 15:44:00 → ORD 2026-12-28 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-12-27 15:44:00 → SFO 2026-12-27 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-12-27 18:42:00 → ORD 2026-12-28 00:59:00.

Explore this route

• All dates for this route
• Dec 26, 2026 · Return options
• Dec 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Dec 27, 2026 · one way: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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